2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:183875-06-1
Molecular Formula:C₃₁H₄₁N₃O₁₄S
Molecular Weight:711.744
Hs Code.:

2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 13 articles about 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 3282-30-2
pivaloyl chloride

: 183875-24-3
Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4R,5S,6R)-3-azido-5-hydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-3-yl ester

: 183875-06-1
2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With pyridine; at 25 ℃; for 2h;
DOI:10.1021/ja9608555

Reference yield:

: 16758-34-2
1-thiophenyl-β-D-galactopyranoside

: 183875-06-1
2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 4-dimethylaminopyridine, pyridine / 24 h / Ambient temperature

2: 96 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 0.25 h / -78 °C

3: 1.) Tf₂O, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, from -60 to -30 deg C, 40 min

4: LiOH*H₂O / methanol / 25 °C

5: 4-aminopyridine, pyridine / 2 h / 25 °C

6: 85 percent / TFA / CH₂Cl₂ / 1 h / 25 °C

7: 92 percent / pyridine / 2 h / 25 °C

With pyridine; 4-aminopyridine; dmap; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/ja9608555

Reference yield:

: 13992-16-0,23661-28-1,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1,24404-53-3
1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

: 183875-06-1
2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-azido-3-hydroxy-6-phenylsulfanyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: NaOMe / methanol / 25 °C

2: 4-dimethylaminopyridine, pyridine / 24 h / Ambient temperature

3: 96 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 0.25 h / -78 °C

4: 1.) Tf₂O, 2.) 2,6-di-tert-butyl-4-methylpyridine / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, from -60 to -30 deg C, 40 min

5: LiOH*H₂O / methanol / 25 °C

6: 4-aminopyridine, pyridine / 2 h / 25 °C

7: 85 percent / TFA / CH₂Cl₂ / 1 h / 25 °C

8: 92 percent / pyridine / 2 h / 25 °C

With pyridine; 4-aminopyridine; dmap; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; sodium methylate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/ja9608555